title: Efficient, stereodivergent access to 3-piperidinols by traceless P(OEt)3 cyclodehydration.
abstract: A stereodivergent and highly diastereoselective (dr up to >19:1 for both isomers), step economic (5-6 steps), and scalable synthesis (up to 14 g) of cis- and trans-2-substituted 3-piperidinols, the core motif of numerous bioactive compounds, providing efficient access to the NK-1 inhibitor L-733,060 is presented. Additionally, a "traceless" (referring to the simplified byproduct separation) cyclodehydration realizing simple P(OEt)3 as a substitute for PPh3 is developed.
authors.affiliation: Aalto University , School of Chemical Technology, Laboratory of Organic Chemistry, Kemistintie 1, 00076 Espoo, Finland.
authors.forename: Peter H
authors.initials: PH
authors.lastname: Huy
authors.forename: Ari M P
authors.initials: AM
authors.lastname: Koskinen
mesh_terms: D003500:Cyclization; D003681:Dehydration; D007659:Ketones / Q000138:chemical synthesis / Q000737:chemistry; D015394:Molecular Structure; D017905:Phosphites / Q000737:chemistry*; D010880:Piperidines / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D007659:Ketones; D017905:Phosphites; D010880:Piperidines